Due to the "handedness" of the molecules of life, the development of efficient methods for stereoselective organic synthesis is essential for the expeditious discovery of new therapeutic compounds. This research program focuses on the development of enantioselective nucleophilic catalysts. Because nucleophiles catalyze an enormous array of useful reactions, work in this area provides the opportunity to develop catalysts that will effect a wide range of processes with high levels of enantioselectivity. This investigation is comprised of two areas of research: (1) the synthesis of new families of planar-chiral nucleophilic catalysts. and (2) the development of enantioselective processes catalyzed by these planar-chiral catalysts. It is anticipated that useful new methods for stereoselective organic synthesis will emerge from this investigation.